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Stewart

$128+ Cheap flights from Pittsburgh to New Windsor (PIT - SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SWF
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Pittsburgh to Stewart

Cheapest flights from Pittsburgh to Stewart
Explore the most affordable flight options available from Pittsburgh to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/111:38 am
PIT
-
SWF
1 stop7h 18m
Multiple Airlines
Sat 6/612:05 pm
SWF
-
PIT
1 stop28h 01m
Multiple Airlines
Deal found 1/26$330
This Kiwi.com deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:00 pm
PIT
-
SWF
1 stop16h 38m
Multiple Airlines
Sun 7/126:30 pm
SWF
-
PIT
1 stop28h 17m
Multiple Airlines
Deal found 1/25$369
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/811:33 am
PIT
-
SWF
1 stop7h 03m
Multiple Airlines
Wed 6/2412:05 pm
SWF
-
PIT
1 stop28h 01m
Multiple Airlines
Deal found 1/27$379
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/16:00 am
PIT
-
SWF
1 stop28h 19m
Multiple Airlines
Sun 2/86:49 pm
SWF
-
PIT
2 stops38h 51m
Multiple Airlines
Deal found 1/27$419
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:47 pm
PIT
-
SWF
1 stop17h 48m
Multiple Airlines
Mon 8/35:49 pm
SWF
-
PIT
1 stop4h 58m
Multiple Airlines
Deal found 1/27$459
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:33 am
PIT
-
SWF
1 stop7h 03m
Multiple Airlines
Sun 6/79:38 am
SWF
-
PIT
1 stop13h 51m
Multiple Airlines
Deal found 1/27$466
This Kiwi.com deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:38 am
PIT
-
SWF
1 stop7h 13m
Multiple Airlines
Mon 5/2512:15 pm
SWF
-
PIT
1 stop24h 40m
Multiple Airlines
Deal found 1/25$482
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:45 am
PIT
-
SWF
2 stops11h 27m
Multiple Airlines
Thu 2/2611:52 am
SWF
-
PIT
1 stop8h 22m
Multiple Airlines
Deal found 1/27$483
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1211:33 am
PIT
-
SWF
1 stop7h 03m
Multiple Airlines
Sat 6/206:45 pm
SWF
-
PIT
1 stop22h 21m
Multiple Airlines
Deal found 1/27$485
This Booking.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:49 pm
PIT
-
SWF
1 stop17h 36m
Breeze Airways
Sat 9/1212:05 pm
SWF
-
PIT
2 stops21h 28m
Breeze Airways
Deal found 1/27$494

Find flight deals from Pittsburgh to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$419
(Kiwi.com)

One-way from

$128
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$186
Provider with most accurate pricing for Pittsburgh-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-New Windsor Stewart flights.
Search Deals
From Pittsburgh to New Windsor Stewart
Search Deals
One-way flight from Pittsburgh to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
Use the filters below to find and compare flights from Pittsburgh to New Windsor that are best for you.

Fly from

Pittsburgh

Fly to

Stewart

Route

Depart

Return

Price

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sun 2/1

6:00 am-10:19 am

1 stop28h 19m

New Windsor Stewart

Sun 2/8

6:49 pm-9:40 am

2 stops38h 51m

$419

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sun 2/22

5:45 am-5:12 pm

2 stops11h 27m

New Windsor Stewart

Thu 2/26

11:52 am-8:14 pm

1 stop8h 22m

$483

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 2/11

6:00 am-10:52 am

1 stop28h 52m

New Windsor Stewart

Sun 2/15

11:42 am-11:59 pm

1 stop12h 17m

$499

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 3/12

3:47 pm-9:02 am

1 stop17h 15m

New Windsor Stewart

Thu 3/19

8:40 pm-11:25 pm

1 stop26h 45m

$564

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 3/12

3:47 pm-9:02 am

1 stop17h 15m

New Windsor Stewart

Sun 3/15

8:40 pm-11:27 pm

1 stop26h 47m

$574

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sun 3/1

5:45 am-5:07 pm

2 stops11h 22m

New Windsor Stewart

Sun 3/8

7:27 pm-11:10 pm

1 stop27h 43m

$575

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 2/25

6:00 am-11:02 am

1 stop29h 02m

$128

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 4/1

6:00 am-9:39 am

1 stop27h 39m

$138

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sun 2/1

6:00 am-10:19 am

1 stop28h 19m

$156

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 2/13

9:09 pm-6:39 pm

2 stops21h 30m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 14 results
1
2

Compare providers for flights from Pittsburgh to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pittsburgh to Stewart in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pittsburgh-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pittsburgh-New Windsor flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pittsburgh to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Pittsburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Pittsburgh to New Windsor

What is the cheapest month to book a flight from Pittsburgh to New Windsor?

Currently, April is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $42). Flying from Pittsburgh to New Windsor in December is currently the most expensive (average of $66). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Pittsburgh to New Windsor?

    Allegiant Air can get you from Pittsburgh to New Windsor in just under 17h 15m. Your travel time can differ by up to . The distance from Pittsburgh to New Windsor is about 327 mi.

  • Can I find deals for flights from Pittsburgh to Stewart that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Stewart.

  • Can I find deals for business class flights from Pittsburgh to Stewart?

    Yes. Cheapflights offers flight deals from Pittsburgh to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pittsburgh to New Windsor?

    Currently, April is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $42). Flying from Pittsburgh to New Windsor in December is currently the most expensive (average of $66). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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